ethyl (E)-2-diazo-4-ethoxycarbonyl-3-trifluoromethylbut-3-enoate | 171290-99-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (E)-2-diazo-4-ethoxycarbonyl-3-trifluoromethylbut-3-enoate
• 英文别名: diethyl 4-diazo-3-trifluoromethylpent-2-enedioate；1,5-Diethyl (2E)-4-diazo-3-(trifluoromethyl)-2-pentenedioate；diethyl (E)-4-diazo-3-(trifluoromethyl)pent-2-enedioate
• CAS: 171290-99-6
• 化学式: C₁₀H₁₁F₃N₂O₄
• 分子量: 280.204
• InChiKey: SYTWWEDFEYFANR-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  54.6
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl (E)-2-diazo-4-ethoxycarbonyl-3-trifluoromethylbut-3-enoate 在 三苯基膦 作用下， 以 乙醚 为溶剂， 以83%的产率得到ethyl 6-ethoxy-4-trifluoromethylpyridazine-3-carboxylate
  参考文献：
  名称：

  New Trifluoromethylated Pyridazines by Reductive Cyclization of Vinyldiazomethanes Bearing a Carbonyl Group

  摘要：

  本文描述了从2-重氮-4,4,4-三氟乙酰乙酸乙酯和Wittig或Horner-Emmons-Wadsworth（HEW）试剂合成新的乙烯基重氮甲烷的过程。带有羰基双键的乙烯基重氮甲烷在三苯基膦的存在下发生还原环化反应，为吡嗪化学提供了新的途径。

  DOI：

  10.1055/s-1995-4041
• 作为产物：
  描述：

  三氟乙酰乙酸乙酯 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 ethyl (E)-2-diazo-4-ethoxycarbonyl-3-trifluoromethylbut-3-enoate
  参考文献：
  名称：

  Chemistry of diazocarbonyl compounds: XXX. Development of a synthetic approach to pyridazine structure via wittig reaction of fluoroalkyl-containing diazo keto esters

  摘要：

  3,4,6-Trisubstituted pyridazines were synthesized from fluoroalkyl-containing diazo keto esters in three steps along two different reaction sequences: (1) Wittig, Staudinger, and diaza-Wittig and (2) Staudinger, Wittig, and diaza-Wittig. According to the first of these with the initial Wittig reaction, the yield of the target 4-fluoroalkyl-substituted pyridazines is almost twice as large as in the reaction sequence involving the corresponding N-phosphanylidene derivatives as intermediates. In both sequences, the final steps (synthesis of vinylphosphazenes and the subsequent diaza-Wittig reaction) occurred as a tandem process, and intermediate vinylphosphazenes could not be isolated. Non-fluorinated diazo keto esters and the respective phosphazenes failed to react with alkoxycarbonylmethylidene(triphenyl)phosphoranes under the same conditions.

  DOI：

  10.1134/s1070428007040203

文献信息

• An efficient synthesis of 3-trifluoromethylated 8-oxabicyclo[3.2.1]octa-2,6-dienes
  作者：Yanli Wang、Shizheng Zhu、Guangyu Zhu、Qichen Huang

  DOI：10.1016/s0040-4020(01)00709-8

  日期：2001.8

  vinyldiazomethanes 3 in the presence of furans resulted in the formation of a series of 3-trifluoromethylated 8-oxabicyclo[3.2.1]octa-2,6-dienes. The 4-substituent on the vinyldiazomethanes had great effects on the product distribution and the stereo- and regiochemistry of the [3+4] annulation products. The rhodium(II) acetate catalyzed reaction of 4-carbonyl substituted vinyldiazomethanes 3a–c with furans resulted

  在呋喃存在下，乙酸铑（II）催化3-三氟甲基化的乙烯基重氮甲烷3的分解导致形成一系列3-三氟甲基化的8-氧杂双环[3.2.1] octa-2,6-二烯。乙烯基重氮甲烷上的4-取代基对产物分布以及[3 + 4]环化产物的立体和区域化学有很大影响。4-羰基取代的乙烯基重氮甲烷3a - c与呋喃的乙酸铑（II）催化反应生成环丙烯和[3 + 4]环化产物，而在氰基取代的乙烯基重氮甲烷3d的情况下，仅获得环加成产物。推测该反应遵循串联环丙烷化/ Cope重排机制。